N-alkali metal-n, n-dihalogen acylsulphanilamides



against certain .types of. bacteria.

, halogen;

Patented Aug. 31, 1943 N -ALKALI METAL-NhNt-DIHALOGENACYLSULPHANILAMIDES Martin Everett Hultquist,--Plainfield, and- Moses L.Crossley,'Bound Brook, N. .J.,';assignors to American Cyanamid Company.New York, N. Y.. a corporation of Maine NoDrawing. Application July 2,1942,

' Serial No. 449,476

9 Claims.

This .inventionrelates to a new type of sulphanilamide derivativecontaining active. halogen.

The activity of sulphanilamide against many bacteria has rendered itdesirable to utilize it as an antiseptic. However,,the action ofsulphanilamide is selective and it is eifective only Derivatives havebeen sought which would have more general antiseptic or germicidalaction. It is;to this type of derivative that the present inventionrelates.

According to the present invention -N -acylsulphanilamides are producedcontaining active These compounds have germicidal action which is notsharply'selective as in the case of sulphanilamide. The compounds of thepresent invention may be considered as N -alkali metal N ,N -dihalogen N-acylsulphanilamides of p the following formula:

Hal

Hal Me in which R isra hydrocarbon radical, Hal is an active halogensuch as chlorine or bromine, and Me is an alkali metal. The compoundsare quite soluble which is another important characteristic of practicalgermicides. For the sake of cheapness, the chlorine and sodium compoundsare preferred, although the bromine compounds are equally effective and,of course, the other alkali metal compounds such as the potassiumcompounds are of substantially the same solubility and effectiveness. Rmay be a hydrocarbon radical of the aliphatic or aryl series, but forbest results it should be an aliphatic radical having a moderate numberof carbon atoms, the compounds where R is C3H1 being preferred. Theproduct claims are not intended to be limited to any particular methodof preparation, but in a more specific aspect a preferred processconsists of treating N -acylsulphanilamide with an alkali metalhydrochloride.

The invention will be described in greater detail in conjunction withthe following specific examples in which the parts are by weight.

EXAMPLE 1 N -sodium-N fl -dichloro-N -butanoylsulphanilamide c1omornomooN-Osom I 01 Na 36 parts of N -butanoyl sulphanilamide are addedto 300 parts of sodium hypochlorite solution containing 12% of activechlorine. A clear solution results and oncooling to 10 C. crystalsseparate out and are filtered off. The solid is then dissolved in about500 parts of Water at C., the solution filtered and 150 parts ofsaturated salt solution added. On cooling to 10 C. filtering and washingwith cold saturated sodium chloride solution, a crystalline .product isobtained in the form of light tan needles. The product does not have anysharp melting point as it decomposes on melting at about -150 C.Titration for active chlorine with sodium thiosulphate after addingpotassium iodide and acetic, acid shows about-98% purity. The product iscontaminated with a small amount of sodium chloride.

EXAMPLE 2 N -sodium-N ,N -dichloro-N -acetylsulphanilamide Cl Na 107parts N -acetylsulphanilamide are slurried in 250 parts of water, and tothis is added a 350 part portion of sodium hypochlorite solutioncontaining 12% active chlorine, maintaining the temperature at 20-25with cooling in a water bath. A light brown solution results, and onstanding, leaf-like crystals separate and are filtered oil.

The solid is dissolved in 300 parts of water at 60, the solution isfiltered and cooled to 10, and the crystals are filtered and Washed witha little ice-cold water. The almost colorless crystals are dried in avacuum dessicator.

Titration of a sample for active chlorine with sodium thiosulphate afterdissolving in water and treating with potassium iodide and acetic acidshows 99.5% purity. The product does not have any sharp melting point,but decomposes vigorously at 200-210 C.

EXAMPLE 3 N -sod ium-N ,N -dichZoro-N -benzoylsulphanilamide 84 parts ofN -benzoylsulphanilamide are slurried in 200 parts water, and to this isadded a 300 part portion of sodium hypochlorite solu- The solid isdissolved in 500 parts of The wet f Titration, 10

in which R is a hydrocarbon radical and Me is an alkali metal.

4. N -alkali metal N ,N dichloro N acylsulphanilamide having thefollowing probable formula:

Rr-G o NOS OQN/ in-which: R1 is an alkyl radical, and Me is an alkalimetal.

and acetic acid shows 99.4% purity. The product. does not, show anysharp melting point, I but.

darkens gradually at ISO-160 and decomposes Weclaim:

1. N -alkali metal-N ,N sulphanilamide having the following probableformula:

Hal

7 Hal Me in which R is a hydrocarbon radical, Hal is a member of thegroup consisting of chlorine and bromine, and Me is an alkali metal.

2. N -a1kali metal N ,N dihalogen-N -acylsulphanilamide having thefollowing probable formula: r

'/Hal RFCQIFOSO N Hal 7 Me in which R1 is an alkyl radical, Hal is amember of the group consisting of chlorine or bromine, and Me is analkali metal. a

3, N -alkali metal N ,N dichloro N acylsulphanilamide having thefollowing probable formula:

RG ONOS o N dihalogen-N -acy I v N5. :N sodium N N dichloro Nbutanoylsulphanilamide having the following probable formula:

omon on oonOso r 6. N -sodium N ,N -dich1oro N -acetylsulp anilamidehaving. the following probable formula: V 1 l CHaC ON SO N l Na ' -'l.N1 -s0dium-N ,N -dichloro-N -benzoylsulphanilamide formula:

' o1 Na having the following probable SpA method of preparing N -alka1imetal- N ,N -diha1ogen-N -acylsulphanilamide which comprises reactingthe corresponding N -acylsulphanilamide with an alkali metal hypohalite.

9. A method of preparing -N -alkali metal- N ,N dichloro Nacylsulphanilamide' which comprises reacting the corresponding N-acylsulphanilamide with an alkali metal hypoohlorite.

MARTIN EVERETT HUL'IQUIST.

- osEsnoRossLEY.

